The 2008 Walk with Israel took place on Sunday, 25 May 2008. It was chaired by Ruth Ekstein and Helen Silverstein. The walk director at UJA was Michelle Golfman, who was assisted by staff Ellen Drazner, Shimmy Wenner, and Elena Livertovsky. In the wake of recent rocket attacks from Gaza, a portion of the $500,000 raised was earmarked for children and their families in Sderot and the Western Negev. New to the walk this year was an inter-school competition to raise the most money. There were many incentives and the "top sixty" were recognized in honour of Israel's sixtieth birthday. A new and major sponsor of the walk this year was "yogen fruz."
The day began with a kick-off party in Coronation Park, then followed a square route around downtown Toronto as far north as Dundas Street, and returned to the lakefront for the RioCan Carnival at the Direct Energy Centre at Exhibition Place. A shorter route, ending at the first rest stop, formed the Bubbie Zaidie Walk. The crowd numbered more than fifteen thousand and included Stéphane Dion, leader of the Liberal Party of Canada, and Peter Shurman, MPP.